KR880000593A - Method for preparing L-2-amino-4- (hydroxymethylphosphinyl) -butyric acid - Google Patents

Abstract

A new process of producing L-2-amino-4-(hydroxymethylphosphinyl)-butyric acid (L-AMPB) is now provided, in which 4-(hydroxymethylphosphinyl)-2-oxo-butyric acid (OMPB) is treated with one or more transaminases or with one or more microorganisms capable of producing the transaminase, in the presence of one or more amino-donor compounds such as alpha -amino acids. According to this process, the optically active L-AMPB useful as herbicidal agent can be produced efficiently in a facile way for a reasonable reaction time.

Description

Method for preparing L-2-amino-4- (hydroxymethylphosphinyl) -butyric acid

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Claims (18)

4- (hydroxy methyl phosphinyl) -2-oxo-butyric acid of formula (II) to one or more transaminases in the presence of one or more amino-donors, or one or more trans A process for preparing L-2-amino-4- (hydroxy methyl phosphinyl) -butyric acid according to formula (I), characterized by treatment with one or more microorganisms capable of producing aminase. The method according to claim 1, wherein the microorganisms used are actinomycetes. The method of claim 1, wherein the microorganism used is a bacterium. The method according to claim 1, wherein the microorganism used is yeast. The method according to claim 1, wherein the microorganisms used are fungus. According to claim 2, wherein the microorganisms used are Streptomyces genus, Streptoticillum genus, Nocardia genus, Nocardiopsis genus, saccakaropopo Said method characterized in that the actinomycetes selected from the genus lyspora, genus catasatosporia, micromonospora and Streptosporangium. According to claim 3, wherein the microorganisms used are of the genus Bacillus, Micrococcus, Staphylocoecus, Escherichia, Pseudomonas, Ceratia. Said method characterized in that the bacteria selected from the genus (serratia) and Corynebacterium (corynebacterium). The genus according to claim 4, wherein the microorganisms used are genus Saccharomyces, Candida genus, Cryptococcus genus, Debaryomyces genus, Trigonopsis genus and Hanssem. Said method characterized in that the yeast (Yeast) selected from the genus Hansenula. The method according to claim 5, wherein the microorganisms used are Genus Aspergillus, Genus Mucor, Aureobasidium genus, Caetomium genus, Penieillium genus and The method characterized in that the fungus (fungus) selected from the genus gliocladium (gliocladium). The method of claim 1, wherein the transaminase used is a glutamic acid-oxaloacetic acid-transaminase, glutamic acid-pyruvic acid-transaminase and 4- (hydroxymethylphosphinyl) -2-oxo-butyric acid as an amino donor. And any one or combination of one or more of the transaminases which can be converted to L-2-amino-4- (hydroxymethylphosphinyl) -butyric acid in the presence of glutamic acid. The method according to claim 1, wherein the amino donor used is glutamic acid and / or aspartic acid. The method of claim 1, wherein 4- (hydroxymethylphosphinyl) -2-oxo-butyric acid is reacted with 4- (hydroxymethylphosphinyl) -2- in an alkali state at a temperature of room temperature-60 ° C and pH7.5-9.0. The method characterized in that the treatment or reaction with at least one transaminase in the presence of at least one amino donor compound in a water-soluble reaction solution in which oxo-butyric acid; amino donor compound and transaminase dissolved. The 4- (hydroxymethylphosphinyl) 2-oxo-butyric acid according to claim 1, wherein the 4- (hydroxymethylphosphinyl) -2- is used in an alkali state at room temperature of -60 ° C and pH7.5-9.0. Treatment with at least one microorganism capable of producing at least one transaminase in the presence of at least one amino donor compound in an aqueous reaction medium solution in which the oxo-butyric acid and amino donor compound are dissolved and the cells of the microorganism are suspended Or reacting. The 4- (hydroxymethylphosphinyl)-according to claim 1, wherein the 4- (hydroxymethylphosphinyl) -2-oxo-butyric acid is subjected to 4- (hydroxy-methylphosphinyl) Containing 2-oxo-butyric acid, amino donor compound and transaminase It is possible to produce at least one transaminase in the presence of at least one amino donor compound in an aqueous reaction medium solution in which the microbial extract is dissolved. The method characterized in that the treatment with microbial extract. The method according to claim 15, wherein the 4- (hydroxymethylphosphinyl) -2-oxo-butyric acid is dissolved in an aqueous reaction medium solution at an initial concentration of 0.1-100 mg / ml of the acid. The method according to claim 1, wherein the 4- (hydroxymethylphosphinyl) -2-oxo-butyric acid and amino donor compound are used, and 4- (hydroxymethylphosphinyl) -2-oxo-butyric acid is selected from L-2-amino-. Wherein said molar ratio is initially in the range of 1: 10-10: 1 in the aqueous reaction medium solution before conversion to 4- (hydroxymethylphosphinyl) -butyric acid. The method according to claim 1 or 13, wherein the 4- (hydroxymethylphosphinyl) -2-oxo-butyric acid and amino donor compound are added to a microbial culture medium capable of producing the transaminase, intactcells) and then 4- (hydroxymethylphosphinyl) -2-oxo-butyric acid, an amino donor compound and the microorganisms interacting with each other. The microorganism of claim 1, wherein the used microorganism capable of producing torsion aminase is Streptomyces hygro scopicus SF-1293 FERM BP-130 or ATCC 21705, Streptomyces hygrosocopicus NP. -50 FERM BP-1368, Streptomyces lividans 66 FERM BP-737, Streptomyces albus IFO 13014 (ATCC 3004), Streptomyces griseus IFO 12875 (ATCC 23345) Streptovericillium cinnamoneum IFO 12852 (ATCC 11874), Streptomycess morookaensis IFO 13416 (ATCC 19166), Nocardia mediterranei ATCC 21271, Noc Cardiopsis dassonvillei JCM 3237, saccharopolyspora hirsuta JCM 3170, (ATCC 278757), Streptomyces virion Streptomyces viridochromogenes IFO 13347 (ATCC 14925), Streptomyces viridochromogenes JCM 4977, Streptomyces pilosus IFO 12807 (ATCC 19797), Micromonospora carbonaceae NRRL 2972 (ATCC 27114), Streptosporangium pseudovulgare ATCC 27100; Bacillus subtillis ATCC 6633, Micrococcus luteus ATCC 9341, Staphylococcus aureus Staphylococcus aureus 209p ATCC 6538, Escherichia coli ATCC 10798, Pseudomonas aeruginosa ATCC 10145, Pseudomonas cepacia ATCC 17759, Setratia marcessen ATCC 13880, Corynebacterium glutamicum ATCC 13032; Saccharomyces cerevisiae ATCC 9763, Candi Candida albicans IAM 4888, Candida albican IAM 4829, cryptococcus neoformans IAM 4772, Debaryomyces hansenii IAM 4356, Trigonopsis variabilis ) IAM 4443, Hansenula schneggi IAM 4269; Aspergillus blavus ATCC 9643 Aspergillus terreus IAM QM 82 J, Muco spinescens IAM MU 3, Aureobasidium pullulans IAM F 24, Cathotomium globosum ATCC 6205, penicillium funiculosum ATCC 9644 and gliocladium virens ATCC The method of 9645. ※ Note: The disclosure is based on the initial application.